Process of making phenol esters.



UNITED STATES PATENT oEEIoE.

FIN SPARRE, OF WILMINGTON, DELAWARE, ASSIGNOR TO THE E. I. DU

PONT DE NEMOURS POWDER COMPANY, OF l/VILMINGTON, DELA- WARE, ACORPORATION OF NEW JERSEY.

PROCESS OF MAKING PH ENOL ESTERS.

Specification of Letters Patent.

Patented Aug. 15, 1905.

Application filed June 1, 1905. Serial No. 263,338.

Tr.- aZZ whom it may concern.-

Be it known that I, FIN SPARRE, a subject of the King of Sweden andNorway, residing at Wilmington, county of Newcastle, and State ofDelaware, have invented a new and useful Improvement in Processes ofMaking Phenol Esters, of which the following is a full, clear, and exactdescription.

The object of the invention is to cheapen the manufacture of phenolester by a new mode of utilizing in its manufacture a chlorin halogencompound.

It is known that phenol ester can be made by the reaction between analkaline salt of phenol and a monohalogen compound of hydrocarbon. Thisreaction is, as a rule, a rather difiicult one and has to be performedat a high temperature-say 52.00 centigrade. It is also generallynecessary to use as the halogen compound the iodid or bromid, becausethe chlorid makes the reaction more difficult to perform. The chlorid,however. is the cheapest compound. I have found that this reaction canbe easily accomplished by means of the chloride when in alcoholicsolution.

To explain the process, I will take anisol as an example. Oaustic'sodiumor caustic potash is dissolved in commercial alcohol, either ethylalcohol or methyl alcohol, the cheapest being to dissolve the causticsoda in methyl alcohol. To this is then added phenol, in this casecarbolic acid, and in this way phenylate of sodium is formed in thealcoholic solution. The sodium phenylate may also be made by heatingphenol and caustic alkalies together and then dissolving the product inalcohol.

This solution is then preferably heated so that the alcohol boils, atemperature of about 70 centigrade being the best in this case, andmethyl chlorid is passed into the solution.

tion of anisol is as follows:

(Phenylate (Methyl of sodium.) chlorid.)

CtHsOOII NaOl (AnisoL) (Sodium chlorid.)

After the reaction the alcohol may be evaporated OH to use over againand the oily liquid, composed mostly of anisol, run to an apparatuswhere it may be distilled with steam for purifying or also distilleddirectly. The sodium chlorid formed during the reaction and separatedcan be used over again for making methyl chlorid.

Having now fully described my invention, what I claim, and desire toprotect by Letters Patent, is

1. The improved process of making phenol esters consisting in dissolvingcaustic alkalies and phenol in alcohol and passing into this alcoholicsolution of alkaline phenylate the halogen hydrocarbon compoundcorresponding to the alcohol group which is intended for the phenolester. 2. The improved process of making anisol by means of the reactionbetween methyl chlorid and an alkaline phenylate in alcoholic so lution.

In testimony of which invention I have hereunto set my hand, atPhiladelphia, on this 26th day of May, 1905.

FIN SPARRE. Witnesses:

M. M. HAMILTON, THoRNL Y B. W 00]).

